1 Structure And Bonding 2 Acids And Bases 3 Introduction To Organic Molecules And Functional Groups 4 Alkanes 5 Stereochemistry 6 Understanding Organic Reactions 7 Alkyl Halides And Nucleophilic Substitution 8 Alkyl Halides And Elimination Reactions 9 Alcohols, Ethers, And Related Compounds 10 Alkenes 11 Alkynes 12 Oxidation And Reduction 13 Mass Spectrometry And Infrared Spectroscopy 14 Nuclear Magnetic Resonance Spectroscopy 15 Radical Reactions 16 Conjugation, Resonance, And Dienes 17 Benzene And Aromatic Compounds 18 Reactions Of Aromatic Compounds 19 Carboxylic Acids And The Acidity Of The O-h Bond 20 Introduction To Carbonyl Chemistry; Organometallic Reagents; Oxidation And Reduction 21 Aldehydes And Ketones-nucleophilic Addition 22 Carboxylic Acids And Their Derivatives-nucleophilic Acyl Substitution 23 Substitution Reactions Of Carbonyl Compounds At The α Carbon 24 Carbonyl Condensation Reactions 25 Amines 26 Carbon–carbon Bond-forming Reactions In Organic Synthesis 27 Pericyclic Reactions 28 Carbohydrates 29 Amino Acids And Proteins 30 Lipids 31 Synthetic Polymers expand_more
Chapter Questions expand_more
Problem 9.1P: Draw all constitutional isomers having molecular formula C4H100. Classify each compound as a 1, 2,... Problem 9.2P Problem 9.3P: Give the IUPAC name for each compound. Problem 9.4P: Problem 9.3 Give the structure corresponding to each name.
Problem 9.5P Problem 9.6P: Name CH33COCH3, a gasoline additive commonly referred to as MTBE, as an alkoxy alkane. Problem 9.7P: Name each epoxide.
a. (two ways) b. c. (two ways)
Problem 9.8P: Problem 9.6 Rank the following compounds in order of increasing boiling point.
Problem 9.9P: Which mechanism is favored by the use of crown ethers in nonpolar solvents, SN1orSN2? Problem 9.10P: Draw the organic product of each reaction. Problem 9.11P Problem 9.12P Problem 9.13P Problem 9.14P Problem 9.15P: Problem 9.13 Draw the structure of each transition state in the two-step mechanism for the... Problem 9.16P: What other alkene is also formed along with Y in Sample Problem 9.3? What alkenes would form from X... Problem 9.17P Problem 9.18P: Explain how the reaction of CH32CHCHCl CH3 with H2O yields two substitution products,CH32CHCHOH CH3... Problem 9.19P Problem 9.20P: Draw the products of each reaction, indicating the stereochemistry around anystereogenic centers. Problem 9.21P: Problem 9.19 What is the major product formed when each alcohol is treated with ?
a. b. c.
Problem 9.22P Problem 9.23P Problem 9.24P: Problem 9.22 Draw the organic products formed in each reaction, and indicate the stereochemistry of... Problem 9.25P: Problem 9.23 Draw two steps to convert into each of the following compounds
and .
Problem 9.26P: Draw the products of each reaction, and indicate the stereochemistry at any stereogenic center. Problem 9.27P: Draw the products of each reaction, and include the stereochemistry at any stereogenic center in... Problem 9.28P: Draw the products formed when (S)-butan-2-ol is treated with TsCl and pyridine, followed by... Problem 9.29P Problem 9.30P Problem 9.31P: Explain why the treatment of anisole with HBr yields phenol and CH3Br, but not bromobenzene. Problem 9.32P Problem 9.33P: The cis and trans isomers of 2, 3-dimethyloxirane both react with OH to give butane-2, 3-diol. One... Problem 9.34P: Problem 9.36 Draw the product of each reaction.
a. c.
b. d.
Problem 9.35P: 9.37 Name each compound depicted in the ball-and-stick models.
a. b. c.
Problem 9.36P: Answer each question using the ball-and-stick model of compound A.
a. Give the IUPAC name for A,... Problem 9.37P Problem 9.38P: a. Draw the structure of 1, 2, and 3 alcohol with molecular formula C4H8O. b. Draw the structure of... Problem 9.39P: Give IUPAC name for each alcohol. a. (CH3)2CHCH2CH2CH2OHd. f. b. (CH3)2CHCH2CH(CH2CH3)CH(OH)CH2CH3e.... Problem 9.40P: Name each ether and epoxide. a.b.c.d. Problem 9.41P Problem 9.42P: Draw the eight constitutional isomers with molecular formula C5H12O that contain an OH group. Give... Problem 9.43P: Rank each group of compounds in order of: a. increasing boiling point: CH3CH2CH2OH, CH32CHOH,... Problem 9.44P Problem 9.45P: 9.44 Why is the boiling point of higher than the boiling point of
( vs. )? Why do both diols... Problem 9.46P: Draw the organic products formed when CH3CH2CH2OH is treated with each reagent. a. H2SO4d. HBrg.... Problem 9.47P: Draw the organic products formed when 1-methyl cyclohexanol is treated with each reagent. In some... Problem 9.48P: What alkenes are formed when each alcohol is dehydrated with TsOH? Label the major product when a... Problem 9.49P Problem 9.50P Problem 9.51P: 9.48 Draw the products of each reaction and indicate stereochemistry around stereogenic centers.
Problem 9.52P Problem 9.53P: 9.52 Draw a stepwise mechanism for the following reaction.
Problem 9.54P: 9.53 Although alcohol V gives a single alkene W when treated with , three isomeric
alkenes (X–Z)... Problem 9.55P Problem 9.56P Problem 9.57P Problem 9.58P: When CH3CH2CH2CH2OH is treated with H2SO4 NaBr, CH3CH2CH2CH2Br is the major product, and... Problem 9.59P: 9.57 Draw a stepwise, detailed mechanism for the following reaction.
Problem 9.60P Problem 9.61P: Draw two different routes to each of the following ethers using a Williamson ether synthesis.... Problem 9.62P Problem 9.63P Problem 9.64P: 9.62 Draw a stepwise mechanism for each reaction.
a.
b.
Problem 9.65P: Draw a stepwise, detailed mechanism for the following reaction.
Problem 9.66P Problem 9.67P: Draw the products of each reaction. a.c. b.d. Problem 9.68P: When each halohydrin is treated with, a product of molecular formula is formed. Draw the structure... Problem 9.69P Problem 9.70P: Devise a stepwise mechanism for the following reaction. Problem 9.71P: Draw the products of each reaction, and indicate the stereochemistry where appropriate. a. f bg. c.... Problem 9.72P: Prepare each compound from CH3CH2CH2CH2OH. More than one step may be needed. a. CH3CH2CH2CH2Brb.... Problem 9.73P: Prepare each compound from cyclopentanol. More than one step may be needed.
a. b. c. d.
Problem 9.74P: 9.72 Identify the reagents (a–h) needed to carry out each reaction.
Problem 9.75P Problem 9.76P: 9.74 Treatment of with affords compound A and . Treatment of under the same conditions forms... Problem 9.77P Problem 9.78P Problem 9.79P: 9.77 Draw a stepwise, detailed mechanism for the following reaction.
Problem 9.80P: Dehydration of 1, 2, 2-trimethylcyclohexanol with H2SO4 affords 1-tert-butylcyclopentene as a minor... Problem 9.81P Problem 9.82P: 9.80 Draw a stepwise mechanism for the following reaction.
Problem 9.83P:
9.81 Aziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides,... format_list_bulleted